


Jack Kelly's Bowery Boys

by HideAmongTheRoses



Series: The Notorious Kelly Mob [1]
Category: Newsies (1992), Newsies - All Media Types, Newsies!: the Musical - Fierstein/Menken
Genre: Aged-Up Character(s), Alternate Universe - Gangsters, Alternate Universe - Mob, Alternate universe - Mafia, Gambling, Gangster Katherine Pulitzer, Implied Violence, Madame Medda, Mafia Don Spot Conlon, Mentions of Prostitution, Mob AU, Mob Boss Davey Jacobs, Mob Boss Jack Kelly, Organized Crime, Prostitution, Turf War, fem!smalls, fem!sniper - Freeform, only by a few years
Language: English
Status: Completed
Published: 2019-03-27
Updated: 2019-03-27
Packaged: 2019-12-18 04:37:24
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,659
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18242519
Author URL: https://archiveofourown.org/users/HideAmongTheRoses/pseuds/HideAmongTheRoses
Summary: Jack Kelly and his gang of ne'er-do-wells, their important friends, and everyone's various roles in his complex operation.Or, I should say, in David Jacobs' operation.





	Jack Kelly's Bowery Boys

The Jack Kelly Gang, the Kelly Athletics Club, the Kelly Mob, Jacobs' Boys, the Bowery Boys. They've been called a lot of things, but they don't really care about the name as long as people understand their control.

Jack Kelly and David “Davey” Jacobs are the notorious duo that run the Manhattan borough. They have eyes on every street, hands in every pot, and they own every person from Harlem to Delancey. They make a fearsome pair. Jack is all about strength and brute force and swift retribution while Davey is much more oriented towards intelligence and power and plays the long game. If you ever end up in trouble with the Kelly Mob, you better pray to God that it was Jack Kelly you wronged and not David Jacobs. Jack will show up sometime within the next few days of your insult - with his top two enforcers, Albert and Tommy Boy, if you're extra special - and beat you to a bloody pulp, maybe he'll even kill you, but anything he does you know will end when he leaves.

Davey's anger is slow. He'll let you stew in your fear while he plans how best to bring you to your knees and once he starts he doesn't stop. To him, no slight is too small, no punishment too severe. He starts with your businesses and he tears them down brick by brick. You’ll be financially ruined before he’s even started. Then it's your reputation, your family, your friends, he pushes and he pushes until all you have is the clothes on your back and the roof over your head and then he burns the roof down.

People don’t cross David Jacobs often.

Charlie “Crutchie” Morris is Kelly’s right-hand man. He’s skinny, with a smile to put the sun to shame and a bum leg, nobody ever really thinks he’s a threat. He’s barely acknowledged in violent situations because people write him off as non-threatening. Nobody ever knows about the heavy pistol tucked under his shirt and hidden from sight behind the crutch. He asks for what he wants sweetly the first time, firmly the second time, and there's never a third. Anyone with half a brain usually complies from the beginning, because his feet might not be fast but you only need one hand to fire a gun. There’s something about him that invites you to test him, though. Something dangerous that beckons for you to give him an excuse to put you in the ground. Maybe it’s the eyes or the smile, or maybe it’s the way one of his hands sits casually on his pistol as he talks. 

All these things are why you never see Jack Kelly out without Crutchie Morris at his side. He acts as Jack, and sometimes Davey’s, personal bodyguard. No one ever suspects him and he follows them everywhere, even into meetings, since no one ever thinks that a cripple is gonna be a threat. They are very very wrong, this kid is faster with a pistol than you can even believe and he never forgets a face. Whenever Davey or Jack are out on business, Crutchie is, without exception, always with them. He has all the patience in the world, but absolutely no tolerance for people who threaten his friends. That bright smile can disappear from his face quick enough to give you whiplash. That is ... if you have time to register it before you've got a bullet somewhere important.

His leg means he isn’t too quick on his feet, but his hands are damn fast.

Antonio "Racetrack" Higgins doubles as the Kelly Gang's most trusted messenger and fixer. As one of the few people with permission onto Don Conlon's territory without repercussion, he often arranges meetings between the Manhattan and Brooklyn boys and spends most of his day at Sheepshead where he rigs horse races, cooks the books, and wastes all of his own money and sometimes the organization's money on unfixed races. He should have learned years ago that being friends with the Don won't get him off light when that week's income is short, but his fingers have been broken so many times they click when they flex and he shows no signs of having learned anything from the experiences. 

Mafia Don Sean "Spot" Conlon is a young man with deadly focus and razor wit who does all the thinking for his pack of Italian boys so they can focus on following up with all the people who think they can get away with not paying him his money. Don't let his stature fool you, Conlon isn't afraid to get his hands dirty and there's a lot of power packed in underneath the cocky grins and expensive cigars. The Conlon Family indisputably owns Brooklyn and Spot's power also allows him to do a lot of what he wants while everyone looks the other way. 

Kid Blink is mostly in charge of directing people, and the closest thing they have to a second in command (or third, if Davey is first and Jack is second). When Jack or Davey says “go deal with this,” Blink decides who goes. He was also a crackshot until he lost his eye, and he doesn't like to talk about how that happened. However, he is able to hit a target from thirty yards with his eyes closed, which is a hell of a party trick. His depth perception is a little off with only one eye, but his muscles still know the movements. It's just a party trick though. He knows in a real situation, nobody's gonna wait for him to square up the shot and close his eye to shoot. He's satisfied with here he is now, albeit more than a little irritable when the urge to go out and do some actual work the way he used to bubbles to the surface. 

Elmer Kasprzak is the sole reason that half the Kelly boys are still alive. He joined the organization at a young age and retained his sunny, childish demeanor for so long that it was quickly agreed that he wouldn't be involved in any of the mob's dealings. Instead, he stays at the lodging house to keep an eye on the younger kids and to patch up the boys who come back soaked. Most of his medical skill is self-taught, but he managed to apprentice with a local veterinarian for a few months and a lot of what he learned carries over. Because money can be tight and the nature of their work, the Kelly boys can't go to the hospital when they need to and Elmer is their solution. He's not naive, though. He knows what they do to bring in cash but they're his family and he cares about them just like they care about him. 

And if he started over in Brooklyn and still visits every few days, nobody thinks twice about it. 

Albert DaSilva and Tommy Boy are Elmer's polar opposites. Together they make up most of Kelly's muscle. Legally, they make their living as professional fighters, but they grew up in that lodging house and when someone needs a soaking they're the ones who get sent.

When Albert's not working or training he's usually with Racetrack, keeping the skinny kid away from trouble or helping him fight his way out of it, and although he can be fairly dramatic and quick to anger, he’s proven time and again that he can take a real beating without complaint. It quickly became an understanding around the house that Albert got hurt all the time, but you only had to worry about him if he stopped complaining. 

Tommy Boy doesn’t talk much and he showed up at the house so young he didn’t know his last name. Behind the broad shoulders and fierce expression, however, is a quick mind that people tend not to notice. He's fiercely loyal and follows most of his directions without question, but there have been times when his steadiness had acted as the wall between Jack's anger and the world until the leader calmed down and rethought his rage-clouded orders. He knows his own strength and he's never lost a fight, but the people Jack and Davey send him out to find don't usually walk away looking too good - sometimes they never walk again - so he makes sure they know what they're doing before he does as he's told. 

Finch works similarly and has a nasty penchant for sending a message. Jack might send Albert or Tommy Boy to get money out of someone, but they send Finch when an example needs to be made. Finch's orders usually include politicians who haven't fulfilled promises or men who overstepped their boundaries. You'd never be able to tell just by talking with him, but there's something in that boy that gets loose sometimes and the people who see it seldom live to tell anyone. 

Mush Meyers has a similar job to Albert and Tommy Boy, although he has a very different approach. In charge of securing bribes, checking on late payments, and otherwise ensuring the people in the pocket of the Kelly Mob stay there, Mush is all easy smiles and charming words and can damn near talk anyone into anything. Mush is a triple threat cause he’s pretty, charismatic, and stubborn as all hell, and he always gets his way. 

The Twins, Mike and Ike Guzman, and the ones who really do the dirty work around town. Jack usually sends Tommy Boy or Albert when he wants someone roughed up or dead, but Davey isn't one for the theatrics and publicity that brings. When he needs someone dead he sends the Twins and whoever it is just disappears. Anyone in Manhattan can tell you there are two Guzman brothers, but as much as the police force want to believe them they have nothing to prove it. It infuriates the law, while Mike and Ike both find it hilarious. 

Buttons and Specs keep the books straight. They keep track of bribes and money owed and will also beat you with said books if you try and screw them over. Specs is in charge of the ledgers, while Buttons counts the physical money and both the books and the cash go in separate safes. They each only know the combination to one, which is both a security measure if one of them gets caught and also a hold-over from when they first started. In the beginning, they didn't trust each other the way they do now, but by now it's a system they have down pat and they're not gonna mess with it after it's worked for so long.

Along with Elmer, JoJo and Henry help keep an eye on the younger boys and new members, showing them the ropes and making sure they keep their noses out of where they aren't wanted. The Kelly Mob has a delicate system in place, no matter how strong they seem, and they aren't about to be sent crashing down cause some new guy knew something he shouldn't and couldn't keep his mouth shut. 

Romeo, Smalls, and Sniper are Davey's little birds. Romeo's slowly getting too tall to function well as a spy and they know it's only a little while before he has to give it up, but he still brings Davey the information he needs when he needs it. Smalls and Sniper are a pair never seen apart if you ever see them. If there's one thing they've learned in their years in the Kelly Mob, it's that people don't pay attention to dirty children, especially when they're girls. If anything happens across the city, there's more than a chance that they know about it, and whenever Davey asks them to find something out it isn't uncommon for them to have the information ready without having to go out and find it. Thanks to them, Davey always knows more than anyone else, is always a step ahead, and sometimes he even knows things about the Conlon Family before Spot does and about the details of Katherine's business deals before they're finalized.

Katherine Pulitzer inherited her empire from her father who left New York a few years ago and hadn't been heard from since, and almost as soon as she gained control she expanded from blackmail to arms deals to double the family fortune. No weapons enter or leave the city through any means other than legal without her say so. She keeps an iron grip on her monopoly and isn't shy about killing the competition. With Bill Hearst and Darcy Reid, they're known in certain circles as The Triad, but there's no debate over the fact that she's in charge. At this point, she has enough money to live honestly until she dies without any changes to her lavish lifestyle, but where's the fun in that? Originally her relationship with the Kelly Mob was strained, but she became much warmer towards them after accidentally being introduced to Davey Jacobs' sister Sarah. Because of Katherine's casual relationship with both Bill and Darcy, Sarah does little more than humor her every once and a while, but it doesn't really matter in the end. They're both quite entertained by the little dance they do. 

Sarah and Les Jacobs are as separate from their brother's work as Davey can get them while still being in his life. With the exceptions of her interactions with Katherine, Sarah keeps herself separate from Davey's work on her own. She does volunteer work when she can and plays an active role in the local Jewish community. Twice a week, usually Tuesdays and Fridays, she hosts a family dinner with her brothers, as well as Jack and Smalls. They can't always make time for dinner together, but they always manage two meals a week together. It's important to Sarah and it's one of the closest things the Kelly siblings have had to a family outside of each other, so it has a priority above a lot of things, which other people don't always understand. 

Les spends his days at school and, although Davey is strict about the rule that Les is not allowed to have any part in the Kelly Mob dealings, the youngest Jacobs spends his afternoons at the lodging house where it seems that everyone knows him and he knows everyone. Smalls has been teaching him some tricks of her trade and Davey is less than thrilled that his little brother now knows how to sneak around undetected and can eavesdrop with the best of them. He blames Jack for it though and is constantly telling him to get his sister to stop corrupting his brother. 

Madame Medda Larkin runs a prestigious playhouse and an infamous brothel, both under the same roof. A lot of her girls used to work the streets, but when they come to her she gives them food and shelter and always lets them decide for themselves which of her establishments they'd rather work in. When Jack and Smalls were little and new to the streets Medda helped them out how she could and they still visit her often. She's one of Jack's most trusted friends, and whenever he's upset there's a good chance he's at the Bowery talking with her or helping her with the sets for her vaudeville shows. With his sway, Jack has been trying to pay her back for her kindness for years but she won't take his money so he finds ways to help her indirectly. At any hour of the day, you can find two or more Kelly boys at the Bowery keeping customers in check and otherwise keeping an eye on Medda and her girls.  

* * *

The status quo in Manhattan is a delicate one, but it manages to balance for years and function relatively smoothly. All the way up until someone decides that the Kelly Mob's control has gone unchallenged for too long. 

**Author's Note:**

> Find more of my Mob AU on my Tumblr, @rosie-anon! I write drabbles, reader inserts, and I'm always excited to answer any questions you might have!
> 
> I don't own Newsies, the characters, or anything of the sort, just the plotline and other original material used to create this alternate universe.
> 
> Not beta'd


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